US2009075978A1PendingUtilityA1
Substituted propiolic acid amides and their use for producing drugs
Est. expiryDec 28, 2025(expired)· nominal 20-yr term from priority
A61P 9/10A61P 43/00A61P 3/04A61P 35/00A61P 27/02A61P 25/30A61P 29/00A61P 25/14A61P 3/00A61P 25/32A61P 25/22A61P 25/34A61P 25/00A61P 25/08A61P 25/06A61P 25/28A61P 25/36A61P 25/16A61P 1/08A61P 21/00A61P 11/00A61P 11/06A61P 17/04C07D 217/06A61P 13/02A61P 1/04A61P 23/00C07D 223/16C07D 209/44C07D 471/04C07D 401/06C07D 487/04C07D 215/08A61P 1/00C07D 209/08A61P 1/12
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Claims
Abstract
The present invention relates to substituted propiolic acid amides, to methods for the production thereof, to medicaments containing these compounds and to the use thereof for producing medicaments.
Claims
exact text as granted — not AI-modified1 . A substituted propiolic acid amides of the formula I,
in which
R 1 denotes unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl;
a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 1, 2, 3, 4, 5 or 6;
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; unsubstituted or substituted alkyl, alkenyl or alkynyl; unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or substituted cycloalkyl or cycloalkenyl; unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
or R 2 and R 3 or R 4 and R 5 or R 6 and R 7 or R 8 and R 9 or R 10 and R 11 or R 12 and R 13 in each case together denote an oxo group (═O) or a thioxo group (═S);
M and W, mutually independently, in each case denote N or C;
P denotes CR 14 , N, NR 15 , O or S;
Q denotes CR 16 , N, NR 17 , O or S;
T denotes CR 18 , N, NR 19 , O or S;
V denotes CR 20 , N, NR 21 , O or S;
g denotes 0 or 1:
wherein M, W; P, Q, T, V and g together form a 5- or 6-membered aromatic or heteroaromatic ring;
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —C(═O)—OH; —C(═O)—H; —NH—C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 2 ; —O—C(═O)—R 29 ; —NH—C(═O)—R 30 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; —NH—C(═O)—NH—R 38 ; —NH—C(═S)—NH—R 39 ; —NH—S(═O) 2 —R 40 ; —NR 41 —S(═O) 2 —R 42 ; unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl; unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted aryl; unsubstituted or at least monosubstituted heteroaryl; unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
R 15 , R 17 , R 19 and R 21 , mutually independently, in each case denote H; —C(═O)—OH; —C(═O)—H; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl; unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted aryl; unsubstituted or at least monosubstituted heteroaryl; unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
and R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 and R 42 , mutually independently, in each case denote unsubstituted or substituted alkyl, alkenyl or alkynyl; unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or substituted cycloalkyl or cycloalkenyl; unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl; or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3, W and M in each case denote C, P denotes CR 14 , Q denotes CR 16 , T denotes CR 18 and V denotes CR 20
with the proviso that compounds are excluded in which g is 0, W and M in each case denote C, P denotes NR 15 , Q denotes CR 16 and T denotes N;
and with the proviso that compounds are excluded in which g is 0, W and M in each case denote C, P denotes N, Q denotes CR 16 and T denotes NR 19 ;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
2 . A compound according to claim 1 , wherein
R 1 denotes unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl; a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 1, 2, 3, 4, 5 or 6; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; unsubstituted or substituted alkyl, alkenyl or alkynyl; unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or substituted cycloalkyl or cycloalkenyl; unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl; or R 2 and R 3 or R 4 and R 5 or R 6 and R 7 or R 8 and R 9 or R 10 and R 11 or R 12 and R 13 in each case together denote an oxo group (═O) or a thioxo group (═S); M and W, mutually independently, in each case denote N or C; P denotes CR 14 , N, NR 15 , O or S; Q denotes CR 16 , N, NR 17 , O or S; T denotes CR 18 , N, NR 19 , O or S; V denotes CR 20 , N, NR 21 , O or S; g denotes 0 or 1: wherein M, W; P, Q, T, V and g together form a 5- or 6-membered aromatic or heteroaromatic ring; R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —C(═O)—OH; —C(═O)—H; —NH—C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —O—C(═O)—R 29 ; —NH—C(═O)—R 30 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; —NH—C(═O)—NH—R 38 ; —NH—C(═S)—NH—R 39 ; —NH—S(═O) 2 —R 40 ; —NR 41 —S(═O) 2 —R 42 ; unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl; unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted aryl; unsubstituted or at least monosubstituted heteroaryl; unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl; R 15 , R 17 , R 19 and R 21 , mutually independently, in each case denote H; —C(═O)—OH; —C(═O)—H; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl; unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted aryl; unsubstituted or at least monosubstituted heteroaryl; unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl; and R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 and R 42 , mutually independently, in each case denote unsubstituted or substituted alkyl, alkenyl or alkynyl; unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or substituted cycloalkyl or cycloalkenyl; unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl; or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl; with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3, W and M in each case denote C, P denotes CR 14 , Q denotes CR 16 , T denotes CR 18 and V denotes CR 20 ; with the proviso that compounds are excluded in which g is 0, W and M in each case denote C, P denotes NR 15 , Q denotes CR 16 and T denotes N; and with the proviso that compounds are excluded in which g is 0, W and M in each case denote C, P denotes N, Q denotes CR 16 and T denotes NR 19 ;
wherein
the above-stated alkyl residues are in each case branched or straight-chain and comprise 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms as chain links;
the above-stated alkenyl residues are in each case branched or straight-chain and comprise 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms as chain links;
the above-stated alkynyl residues are in each case branched or straight-chain and comprise 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms as chain links;
the above-stated heteroalkyl residues, heteroalkenyl residues and heteroalkynyl residues are in each case 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11- or 12-membered;
the above-stated heteroalkyl residues, heteroalkenyl residues and heteroalkynyl residues in each case optionally comprise 1, 2 or 3 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen (NH) and sulfur as chain link(s);
the above-stated alkyl residues, alkenyl residues, alkynyl residues, heteroalkyl residues, heteroalkenyl residues and heteroalkynyl residues may be substituted in each case with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH, —NH 2 , —N(C 1-5 -alkyl) 2 , —N(C 1-15 -alkyl)(phenyl), —N(C 1-5 -alkyl)(CH 2 -phenyl), —N(C 1-5 -alkyl)(CH 2 —CH 2 -phenyl), —C(═O)—H, —C(═O)—C 1-5 -alkyl, —C(═O)-phenyl, —C(═S)—C 1-5 -alkyl, —C(═S)-phenyl, —C(═O)—OH, —C(═O)—O—C 1-5 -alkyl, —C(═O)—O-phenyl, —C(═O)—NH 2 , —C(═O)—NH—C 1-5 -alkyl, —C(═O)—N(C 1-5 -alkyl) 2 , —S(═O)—C 1-5 -alkyl, —S(═O)-phenyl, —S(═O) 2 —C 1-5 -alkyl, —S(═O) 2 -phenyl, —S(═O) 2 —NH 2 and —SO 3 H, wherein the phenyl residues may be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , —OH, —NH 2 , —O—CF 3 , —SH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert.-butyl;
the above-stated cycloalkyl residues in each case comprise 3, 4, 5, 6, 7, 8 or 9 carbon atoms as ring members;
the above-stated cycloalkenyl residues in each case comprise 3, 4, 5, 6, 7, 8 or 9 carbon atoms as ring members;
the above-stated heterocycloalkyl residues are in each case 3-, 4-, 5-, 6-, 7-, 8- or 9-membered;
the above-stated heterocycloalkenyl residues are in each case 4-, 5-, 6-, 7-, 8- or 9-membered;
the above-stated heterocycloalkyl residues and heterocycloalkenyl residues in each case optionally comprise 1, 2 or 3 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen (NH) and sulfur as ring member(s);
the above-stated cycloalkyl residues, heterocycloalkyl residues, cycloalkenyl residues or heterocycloalkenyl residues may be substituted in each case with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , —OH, —NH 2 , —O—CF 3 , —SH, —O—C 1-5 -alkyl, —O-phenyl, —O—CH 2 -phenyl, —(CH 2 )—O—C 1-5 -alkyl, —S—C 1-5 -alkyl, —S-phenyl, —S—CH 2 -phenyl, —C 1-5 alkyl, —C 2-5 alkenyl, —C 2-5 alkynyl, —C═C—Si(CH 3 ) 3 , —C═C—Si(C 2 H 5 ) 3 , —C(═O)—O—C 1-5 -alkyl, —C(═O)—CF 3 , —S(═O) 2 —C 1-5 -alkyl, —S(═O)—C 1-5 -alkyl, —S(═O) 2 -phenyl, oxo (═O), thioxo (═S), —N(C 1-5 -alkyl) 2 , —N(H)(C 1-5 -alkyl), —NO 2 , —S—CF 3 , —C(═O)—OH, —NH—S(═O) 2 —C 1-5 -alkyl, —NH—C(═O)—C 1-5 -alkyl, —C(═O)—H, —C(═O)—C 1-5 -alkyl, —C(═O)—NH 2 , —C(═O)—N(C 1-5 -alkyl) 2 , —C(═O)—N(H)(—C 1-5 -alkyl) and phenyl, wherein the phenyl residue may in each case be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , —OH, —NH 2 , —O—CF 3 , —SH, —O—C 1-5 -alkyl, —O-phenyl, —O—CH 2 -phenyl, —(CH 2 )—O—C 1-5 -alkyl, —S—C 1-5 -alkyl, —S-phenyl, —S—CH 2 -phenyl, —C 1-5 alkyl, —C 2-5 alkenyl, —C 2-5 alkynyl, —C≡C—Si(CH 3 ) 3 , —C≡C—Si(C 2 H 5 ) 3 , —C(═O)—O—C 1-5 -alkyl, and —C(═O)—CF 3 , wherein the above-stated phenyl residues may be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , —OH, —NH 2 , —O—CF 3 , —SH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert.-butyl;
the above-stated alkylene residues are in each case branched or straight-chain and comprise 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms as chain links;
the above-stated alkenylene residues are in each case branched or straight-chain and comprise 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms as chain links;
the above-stated alkynylene residues are in each case branched or straight-chain and comprise 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms as chain links;
the above-stated heteroalkylene residues and heteroalkenylene residues are in each case 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11- or 12-membered;
the above-stated heteroalkylene and heteroalkenylene groups may in each case optionally comprise 1, 2 or 3 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen (NH) and sulfur as chain link(s);
the above-stated alkylene, alkenylene, alkynylene, heteroalkylene or heteroalkenylene group may in each case be unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of phenyl, F, Cl, Br, I, —NO 2 , —CN, —OH, —O-phenyl, —O—CH 2 -phenyl, —SH, —S-phenyl, —S—CH 2 -phenyl, NH 2 , —N(C 1-5 -alkyl) 2 , —NH-phenyl, —N(C 1-5 -alkyl)(phenyl), —N(C 1-5 -alkyl)(CH 2 -phenyl), —N(C 1-5 -alkyl)(CH 2 —CH 2 -phenyl), —C(═O)—H, —C(═O)—C 1-5 -alkyl, —C(═O)-phenyl, —C(═S)—C 1-5 -alkyl, —C(═S)-phenyl, —C(═O)—OH, —C(═O)—O—C 1-15 -alkyl, —C(═O)—O-phenyl, —C(═O)—NH 2 , —C(═O)—NH—C 1-5 -alkyl, —C(═O)—N(C 1-5 -alkyl) 2 , —S(═O)—C 1-5 -alkyl, —S(═O)-phenyl, —S(═O) 2 —C 1-5 -alkyl, —S(═O) 2 -phenyl, —S(═O) 2 —NH 2 and —SO 3 H, wherein the phenyl residues may be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —NO 2 , —OH, —SH, —NH 2 , —C(═O)—OH, —C 1-15 alkyl, —(CH 2 )—O—C 1-5 -alkyl, —C 2-5 alkenyl, —C 2-5 alkynyl, —C≡C—Si(CH 3 ) 3 , —C═C—Si(C 2 H 5 ) 3 , —S—C 1-5 -alkyl, —S-phenyl, —S—CH 2 -phenyl, —O—C 1-5 -alkyl, —O-phenyl, —O—CH 2 -phenyl, —CF 3 , —CHF 2 , —CH 2 F, —O—CF 3 , —O—CHF 2 , —O—CH 2 F, —C(═O)—CF 3 , —S—CF 3 , —S—CHF 2 and —S—CH 2 F;
the above-stated aryl residues are mono- or bicyclic and comprise 6, 10 or 14 carbon atoms;
the above-stated heteroaryl residues are mono-, di- or tricyclic and 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered;
the above-stated 5- to 14-membered heteroalkyl residues optionally comprise 1, 2, 3, 4 or 5 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen (NH) and sulfur as ring member(s);
and the above-stated aryl or heteroaryl residues may optionally in each case be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —NO 2 , —OH, —SH, —NH 2 , —C(═O)—OH, —C 1-5 alkyl, —(CH 2 )—O—C 1-5 -alkyl, —C 2-5 alkenyl, —C 2-5 alkynyl, —C≡C—Si(CH 3 ) 3 , —C—C≡Si(C 2 H 5 ) 3 , —S—C 1-5 -alkyl, —S-phenyl, —S—CH 2 -phenyl, —O—C 1-5 -alkyl, —O-phenyl, —O—CH 2 -phenyl, —CF 3 , —CHF 2 , —CH 2 F, —O—CF 3 , —O—CHF 2 , —O—CH 2 F, —C(═O)—CF 3 , —S—CF 3 , —S—CHF 2 , —S—CH 2 F, —S(═O) 2 -phenyl, —S(═OC) 2 —C 1-5 -alkyl, —S(═O)—C 1-5 -alkyl, —NH—C 1-5 -alkyl, N(C 1-5 -alkyl) 2 , —C(═O)—O—C 1-5 -alkyl, —C(═O)—H, —C(═O)—C 1-5 -alkyl, —CH 2 —O—C(═O)-phenyl, —O—C(═O)-phenyl, —NH—S(═O) 2 —C 1-5 -alkyl, —NH—C(═O)—C 1-5 -alkyl, —C(═O)—NH 2 , —C(═O)—NH—C 1-5 -alkyl, —C(═O)—N(C 1-5 -alkyl) 2 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrazolyl, phenyl, furyl (furanyl), thiazolyl, thiadiazolyl, thiophenyl (thienyl), benzyl and phenethyl, wherein the cyclic substituents or the cyclic residues of these substituents may themselves be substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —NO 2 , —OH, —SH, —NH 2 , —C(═O)—OH, —C 1-5 alkyl, —(CH 2 )—O—C 1-5 -alkyl, —C 2-5 alkenyl, —C 2-5 alkynyl, —C≡C—Si(CH 3 ) 3 , —C═C—Si(C 2 H 5 ) 3 , —S—C 1-5 -alkyl, —S-phenyl, —S—CH 2 -phenyl, —O—C 1-5 -alkyl, —O-phenyl, —O—CH 2 -phenyl, —CF 3 , —CHF 2 , —CH 2 F, —O—CF 3 , —O—CHF 2 , —O—CH 2 F, —C(═O)—CF 3 , —S—CF 3 , —S—CHF 2 and —S—CH 2 F;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvates.
3 . A compounds according to claim 1 , wherein
R 1 denotes a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, furyl, thienyl, pyrazolyl, pyridazinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, imidazolyl, indolyl, benzo[b]thiophenyl, benzo[d]thiazolyl, benzo[b]furanyl, quinolinyl, isoquinolinyl and quinazolinyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —C≡C—Si(CH 3 ) 3 , —C≡C—Si(C 2 H 5 ) 3 , —CH 2 —O—CH 3 , —CH 2 —O—C 2 H 5 , —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—H; —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—NH 2 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 and phenyl.
4 . A compound according to claim 1 , wherein
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 2-6 heteroalkyl, C 2-6 heteroalkenyl or C 2-6 heteroalkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 , or comprises 1 or 2 heteroatom(s) mutually independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as chain link(s); or C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or R 2 and R 3 or R 4 and R 5 or R 6 and R 7 or R 8 and R 9 or R 10 and R 11 or R 12 and R 13 , mutually independently, together in each case denote a residue selected from the group consisting of an oxo group (═O) or a thioxo group (═S).
5 . A compound according to claim 1 , wherein W, M, P, Q, T and optionally V together denote a ring selected from the group consisting of
6 . A compound according to claim 1 , wherein
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —C(═O)—OH; —C(═O)—H; —NH—C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —O—C(═O)—R 29 ; —NH—C(═O)—R 30 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 .
7 . A compound according to claim 1 , wherein R 15 , R 17 , R 19 and R 21 , mutually independently, in each case denote H; —C(═O)—H; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group and/or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 .
8 . A compound according to claim 1 , wherein R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 and R 42 mutually independently, in each case denote C 1-6 alkyl, which is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, pyrrolyl, indolyl, furanyl, benzo[b]furanyl, thiophenyl, benzo[b]thiophenyl, benzo[d]thiazolyl, pyrazolyl, imidazolyl, thiazolyl, thiadiazolyl, triazolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyranyl, indazolyl, quinolinyl, isoquinolinyl and quinazolinyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group and/or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 and —C(═O)—O—C 2 H 5 .
9 . A compound according to claim 1 , wherein
R 1 denotes a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, furyl, thienyl, pyrazolyl, pyridazinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, imidazolyl, indolyl, benzo[b]thiophenyl, benzo[d]thiazolyl, benzo[b]furanyl, quinolinyl, isoquinolinyl and quinazolinyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —C≡C—Si(CH 3 ) 3 , —C≡C—Si(C 2 H 5 ) 3 , —CH 2 —O—CH 3 , —CH 2 —O—C 2 H 5 , —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—H; —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—NH 2 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 and phenyl; a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 1, 2, 3, 4, 5 or 6; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 2-6 heteroalkyl, C 2-6 heteroalkenyl or C 2-6 heteroalkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 or comprises 1 or 2 heteroatom(s) mutually independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as chain link(s); or C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or R 2 and R 3 or R 4 and R 5 or R 6 and R 7 or R 3 and R 9 or R 10 and R 11 or R 12 and R 13 , mutually independently, together in each case denote a residue selected from the group consisting of an oxo group (═O) or a thioxo group (═S; g denotes 0 or 1; W, M, P, Q, T and optionally V together denote a ring selected from the group consisting of
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —C(═O)—OH; —C(═O)—H; —NH—C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —O—C(═O)—R 29 ; —NH—C(═O)—R 30 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH,
oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ;
or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 ;
R 15 and R 17 , mutually independently, in each case denote H; C(═O)—H; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group and/or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 ;
and R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 , mutually independently, in each case denote C 1-6 alkyl, which is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —NO 2 , —CN, —OH, —SH and —NH 2 ; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, oxo, thioxo, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, pyrrolyl, indolyl, furanyl, benzo[b]furanyl, thiophenyl, benzo[b]thiophenyl, benzo[d]thiazolyl, pyrazolyl, imidazolyl, thiazolyl, thiadiazolyl, triazolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyranyl, indazolyl, quinolinyl, isoquinolinyl and quinazolinyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 and —C(═O)—O—C 2 H 5 ;
with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3 and W, M, P, Q, T and V together denote
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
10 . A compound according to claim 1 , wherein
R 1 denotes a residue selected from the group consisting of phenyl, thienyl, pyridazinyl, pyrazinyl, pyrimidinyl, pyridinyl, thiazolyl and thiadiazolyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —C≡C—Si(CH 3 ) 3 , —C═C—Si(C 2 H 5 ) 3 , —CH 2 —O—CH 3 , —CH 2 —O—C 2 H 5 , —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—H; —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—NH 2 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 and phenyl; a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 2, 3, 4, 5 or 6; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; —CH 2 —OH; —CH 2 —NH 2 ; —CH 2 —CN; —CH 2 —CH 2 —OH; —CH 2 —CH 2 —NH 2 ; —CH 2 —CH 2 —CN; —CH 2 —CH 2 —CH 2 —OH; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted; C 2-6 heteroalkyl, C 2-6 heteroalkenyl or C 2-6 heteroalkynyl, which is in each case unsubstituted or comprises 1 or 2 heteroatom(s) mutually independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as chain link(s); or C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —S—CH 3 and —S—C 2 H 5 ; g denotes 0 or 1; W, M, P, Q, T and optionally V together denote a ring selected from the group consisting of
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —C(═O)—OH; —C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —O—C(═O)—R 29 ; —NH—C(═O)—R 30 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted; C 3-7 cycloalkyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —O—CH 3 , —O—C 2 H 5 and —O—C 3 H 7 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 ;
R 15 and R 17 , mutually independently, in each case denote H; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; —C(═O)—H; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted; C 3-7 cycloalkyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —O—CH 3 , —O—C 2 H 5 and —O—C 3 H 7 ; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 ;
and R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 , mutually independently, in each case denote —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; unsubstituted C 1-6 alkyl; C 3-7 cycloalkyl, C 5-6 cycloalkenyl, 5- to 7-membered heterocycloalkyl and 5- to 7-membered heterocycloalkenyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 and —O—C 3 H 7 ; or denote a residue selected from the group consisting of phenyl, naphthyl, furanyl, thiophenyl, pyrazolyl, imidazolyl, thiazolyl, thiadiazolyl, triazolyl, oxazolyl, oxadiazolyl, isoxazolyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 and —C(═O)—O—C 2 H 5 ;
with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3 and W, M, P, Q, T and V together denote
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
11 . A compound according to claim 1 , wherein
R 1 denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —C═C—Si(CH 3 ) 3 , —C≡C—Si(C 2 H 5 ) 3 , —CH 2 —O—CH 3 , —CH 2 —O—C 2 H 5 , —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—H; —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—NH 2 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 and phenyl; a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 2, 3, 4 or 5; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; —CH 2 —OH; —CH 2 —NH 2 ; —CH 2 —CN; —CH 2 —CH 2 —OH; —CH 2 —CH 2 —NH 2 ; —CH 2 —CH 2 —CN; —CH 2 —CH 2 —CH 2 —OH; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted; or denote unsubstituted C 3-7 cycloalkyl; g denotes 0 or 1; W, M, P, Q, T and optionally V together denote a ring selected from the group consisting of
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —O—C(═O)—R 29 ; —NH—C(═O)—R 30 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, which is in each case unsubstituted; unsubstituted C 3-7 cycloalkyl; or denote a residue selected from the group consisting of phenyl, naphthyl, anthracenyl, thienyl, furyl, pyridinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl and isoxazolyl, which may in each case be attached via a C 1-3 alkylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-butyl, —OH, —SH, —NH 2 , —C(═O)—OH, —S—CH 3 , —S—C 2 H 5 , —S(═O)—CH 3 , —S(═O) 2 —CH 3 , —S(═O)—C 2 H 5 , —S(═O) 2 —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CHF 2 , —CH 2 F and —O—CF 3 ;
R 22 , R 23 , R 24 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 and R 35 , mutually independently, in each case denote —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; or denote unsubstituted C 1-6 alkyl;
and R 25 and R 26 , mutually independently, in each case denote CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; unsubstituted C 1-6 alkyl; or denote a residue selected from the group consisting of phenyl, naphthyl, furanyl, pyrazolyl, imidazolyl, thiazolyl, thiadiazolyl, triazolyl, oxazolyl, oxadiazolyl, isoxazolyl and thiophenyl, which may in each case be attached via a C 1-3 alkylene, C 2-3 alkenylene or C 2-3 alkynylene group or is unsubstituted or substituted with optionally 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NH 2 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—CH 3 , —NH—C 2 H 5 , —NO 2 , —CF 3 , —O—CF 3 , —S—CF 3 , —SH, —NH—S(═O) 2 —CH 3 , —C(═O)—OH, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—N(CH 3 ) 2 , —C(═O)—NH—CH 3 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —C(═O)—O—CH 3 and —C(═O)—O—C 2 H 5 ;
with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3 and W, M, P, Q, T and V together denote
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
12 . A compound according to claim 1 , wherein
R 1 denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ; a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 2, 3 or 4; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl; g denotes 0 or 1; W, M, P, Q, T and optionally V together denote a ring selected from the group consisting of
and R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —NH—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3 and W, M, P, Q, T and V together denote
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salts or in each case in the form of a corresponding solvate.
13 . A compound according to claim 1 , wherein
R 1 denotes a residue selected from the group consisting of phenyl, thienyl and pyridinyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 2, 3 or 4; R 2 and R 4 mutually independently, in each case denote H; methyl or ethyl; R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 in each case denote H; g denotes 0 or 1; W, M, P, Q, T and optionally V together denote a ring selected from the group consisting of
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl;
with the proviso that compounds are excluded in which the sum of a, b, c, d, e and f is equal to 3 and W, M, P, Q, T and V together denote
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
14 . A compound of the formula Ia, according to claim 1 ,
in which
R 1a denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2a , R 3a , R 4a and R 5a , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl;
ga denotes 0 or 1;
W a , M a , P a , Q a , T a and optionally V a together denote a ring selected from the group consisting of
and R 14a , R 16a , R 18a and R 20a , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —NH—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
15 . A compound according to claim 14 , wherein
R 1a denotes a residue selected from the group consisting of phenyl, thienyl and pyridinyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; R 2a and R 4a , mutually independently, in each case denote H; methyl or ethyl; R 3a and R 5a , in each case denote H; ga denotes 0 or 1; W a , M a , P a , Q a , T a and optionally V a together denote a ring selected from the group consisting of
and R 14a , R 16a , R 18a and R 20a , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl.
16 . A compound of the formula Ib, according to claim 1 ,
in which
R 1b denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2b , R 3b , R 8b and R 9b , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl and cyclobutyl;
gb denotes 0 or 1;
W b , M b , P b , Q b , T b and optionally V b together denote a ring selected from the group consisting of
and R 14b , R 16b , R 18b and R 20b , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —NH—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
17 . A compound according to claim 16 , wherein
R 1b denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; R 2b , R 3b , R 4b and R 5b , mutually independently, in each case denote H; methyl or ethyl; gb denotes 0 or 1; W b , M b , P b , Q b , T b and optionally V b together denote a ring selected from the group consisting of
and R 14b , R 16b , R 18b and R 20b , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl.
18 . A compound of the formula Ic, according to claim 1 ,
in which
R 1c denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2c , R 3c , R 4c , R 5c , R 8c , R 9c , R 10c and R 11c , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl;
gc denotes 0 or 1;
W c , M c , P c , Q c , T c and optionally V c together denote a ring selected from the group consisting of
and R 14c , R 16c , R 18c and R 20c , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —NH—C(═O)—CH 3 ; —N(CH 3 )—
C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
19 . A compound according to claim 18 , wherein
R 1c denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; R 2a , R 3c , R 4c , R 5c , R 8c , R 9c , R 10c and R 11c , mutually independently, in each case denote H; methyl or ethyl; gc denotes 0 or 1; W c , M c , P c , Q c , T c and optionally V c together denote a ring selected from the group consisting of
and R 14c , R 16c , R 18c and R 20c , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl.
20 . A compound of the formula Id, according to claim 1 ,
in which
R 1d denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2d , R 3d , R 4d , R 5d , R 6d , R 7d , R 8d and R 9d , mutually independently, in each case denote H; F; Cl; Br; i; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl and or cyclobutyl;
gd denotes 0 or 1;
W d , M d , P d , Q d , T d and optionally V d together denote a ring selected from the group consisting of
and R 14d , R 16d , R 18d and R 20d , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —NH—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
21 . A compound according to claim 20 , wherein
R 1d denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; R 2d , R 3d , R 4d , R 5d , R 6d , R 7d , R 8d and R 9d , mutually independently, in each case denote H; methyl or ethyl; gd denotes 0 or 1; W d , M d , P d , Q d , T d and optionally V d together denote a ring selected from the group consisting of
and R 14a , R 16a , R 18a and R 20a , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl.
22 . A compounds according to claim 1 , selected from the group consisting of
[3] 1-(3-phenyl-propiolyl)-2,3-dihydro-indole,
[4] 6-(3-phenyl-propiolyl)-5,6,7,8-tetrahydro-[1,6]naphthyridine,
[6] 2-(3-phenyl-propiolyl)-2,3-dihydro-isoindole,
[8] 3-methyl-5-(3-phenyl-propiolyl)-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine,
[9] 3-phenyl-5-(3-phenyl-propiolyl)-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine,
[10] 7-(3-phenyl-propiolyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine,
3-(3-(3-chlorophenyl)-propiolyl)-1,2,4,5-tetrahydrobenzo[d]azepine,
2-(3-(3-chlorophenyl)-propiolyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine,
7-(3-(3-chlorophenyl)-propiolyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine,
2-(3-(3-chlorophenyl)-propiolyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine,
1-(3-(2,4-difluorophenyl)-propiolyl)-2-methyl-indoline,
1-(3-(4-fluoro-3-methylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(2-fluorophenyl)-propiolyl)-2-methyl-indoline, 1-(3-(4-tolyl)-propiolyl)-2-methyl-indoline,
1-(3-(4-trifluoromethylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-phenyl-propiolyl)-2-methyl-indoline,
1-(3-(2,3-dimethylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(3,5-dimethylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(2,4-dichlorophenyl)-propiolyl)-2-methyl-indoline,
1-(3-(3-tolyl)-propiolyl)-2-methyl-indoline,
1-(3-(4-methoxyphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(2-thienyl)-propiolyl)-2-methyl-indoline,
1-(3-(2,4-dimethylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(4-fluorophenyl)-propiolyl)-2-methyl-indoline,
1-(3-(3-chlorophenyl)-propiolyl)-2-methyl-indoline,
1-(3-(3-fluoro-4-methylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(4-tert.-butylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(3,4-dimethylphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(2-bromo-5-methoxyphenyl)-propiolyl)-2-methyl-indoline,
1-(3-(2-tolyl)-propiolyl)-2-methyl-indoline and
1-(3-(2-trifluoromethylphenyl)-propiolyl)-2-methyl-indoline;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
23 . A compound of the formula Ik, according to claim 1 ,
in which
W denotes Cl, methyl or —CN;
and R 14k , R 16k , R 18k and R 20k , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —NH—C(═O)—CH 3 ; —N(CH 3 )—
C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl or tert.-butyl;
optionally in each case in the form of a corresponding salt or optionally in each case in the form of a corresponding solvate.
24 . A compound according to claim 23 selected from the group consisting of
[5] 2-(3-(3-chlorophenyl)-propiolyl)-1 ,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6,7-dihydroxy-1 ,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6-hydroxy-7-methoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-3-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-7-methoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-8-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-7-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-5-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-7-hydroxy-1,2,3,4-tetrahydro-isoquinoline,
[29] 2-(3-(3-chlorophenyl)-propiolyl)-8-methoxy-1,2,3,4-tetrahydro-isoquinoline,
[30] 2-(3-(3-chlorophenyl)-propiolyl)-5-methoxy-1,2,3,4-tetrahydro-isoquinoline,
[31] 2-(3-(3-chlorophenyl)-propiolyl)-1,8-dimethyl-1,2,3,4-tetrahydro-isoquinoline,
[51] 2-(3-(3-tolyl)-propiolyl)-1 ,2,3,4-tetrahydro-isoquinoline and [77] 2-(3-(3-cyano-phenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline;
in each case optionally in the form of a corresponding salt, or in each case optionally in the form of a corresponding solvate.
25 . (canceled)
26 . A method for producing a compound of the formula I according to claim 1 , said method comprising: reacting at least one compound of the formula II,
in which R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , M, W, P, Q, T, V, a, b, c, d, e, f and g have the meaning according to claim 1 with at least one compound of the formula R 1 —C≡C—C(═O)—OH, in which R 1 has the meaning according to claim 1 , optionally in a reaction medium, optionally in the presence of at least one suitable coupling agent, optionally in the presence of at least one base, or with at least one compound of the formula R 1 —C≡C—C(═O)—X, in which R 1 has the above-stated meaning and X denotes a leaving group, in a reaction medium, optionally in the presence of at least one base, converting the compound into at least one corresponding compound of the formula I, optionally in the form of a corresponding salt,
in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , M, W, P, Q, T, V, a, b, c, d, e, f and g have the above-stated meaning, and optionally purifying the compound or isolating the compound, or both;
or by reacting at least one compound of the formula II with propiolic acid HC≡C—C(═O)—OH] optionally in a reaction medium, optionally in the presence of at least one suitable coupling agent, optionally in the presence of at least one base, or by reaction with at least one compound of the formula HC≡C—C(═O)—X, in which X denotes a leaving group, in a reaction medium, optionally in the presence of at least one base, converting the compound into at least one corresponding compound of the formula III, optionally in the form of a corresponding salt,
in which R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , M, W, P, Q, T, V, a, b, c, d, e, f and g have the above-stated meaning, and optionally purifying the compound or isolating the compound, or both,
and by reacting at least one compound of the formula III with at least one compound of the formula R 1 —X, in which R 1 has the meaning according to claim 1 and X denotes a leaving group, optionally in the presence of at least one catalyst, optionally in the presence of at least one ligand, optionally in the presence of at least one inorganic salt, optionally in the presence of at least one copper salt, optionally in the presence of at least one organic or inorganic base, converting the compound into at least one corresponding compound of the formula I, optionally in the form of a corresponding salt, and optionally purifying the compound or isolating the compound, or both.
27 . A pharmaceutical composition comprising: at least one substituted propiolic acid amide compound of the formula I
in which
R 1 denotes unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl;
a, b, c, d, e and f in each case denote 0 or 1; wherein the sum of a, b, c, d, e and f is equal to 1, 2, 3, 4, 5 or 6;
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; unsubstituted or substituted alkyl, alkenyl or alkynyl; unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or substituted cycloalkyl or cycloalkenyl; unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
or R 2 and R 3 or R 4 and R 5 or R 6 and R 7 or R 3 and R 9 or R 10 and R 11 or R 12 and R 13 in each case together denote an oxo group (═O) or a thioxo group (═S);
M and W, mutually independently, in each case denote N or C;
P denotes CR 14 , N, NR 15 , O or S;
Q denotes CR 16 , N, NR 17 , O or S;
T denotes CR 18 , N, NR 19 , O or S;
V denotes CR 20 , N, NR 21 , O or S;
g denotes 0 or 1:
wherein M, W; P, Q, T, V and g together form a 5- or 6-membered aromatic or heteroaromatic ring;
R 14 , R 16 , R 18 and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —NH 2 ; —OH; —SH; —C(═O)—OH; —C(═O)—H; —NH—C(═O)—H; —NH—R 22 ; —NR 23 R 24 ; —O—R 25 ; —S—R 26 ; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —O—C(═O)—R 29 ; —NR 31 —C(═O)—R 32 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; —NH—C(═O)—NH—R 38 ; —NH—C(═S)—NH—R 39 ; —NH—S(═O) 2 —R 40 ; —NR 41 —S(═O) 2 —R 42 ; unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl; unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted aryl; unsubstituted or at least monosubstituted heteroaryl; unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
R 15 , R 17 , R 19 and R 21 , mutually independently, in each case denote H; —C(═O)—OH; —C(═O)—H; —C(═O)—R 27 ; —C(═O)—O—R 28 ; —C(═O)—NH 2 ; —C(═O)—NH—R 33 ; —C(═O)—NR 34 R 35 ; —S(═O)—R 36 ; —S(═O) 2 —R 37 ; unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl; unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or at least monosubstituted aryl; unsubstituted or at least monosubstituted heteroaryl; unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
and R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 and R 42 , mutually independently, in each case denote unsubstituted or substituted alkyl, alkenyl or alkynyl; unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl; unsubstituted or substituted cycloalkyl or cycloalkenyl; unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl; unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl; unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl; unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl; or -(heteroalkenylene)-heterocycloalkenyl; unsubstituted or substituted aryl; unsubstituted or substituted heteroaryl; unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl; or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
with the proviso that compounds are excluded in which g is 0, W and M in each case denote C, P denotes NR 15 , Q denotes CR 16 and T denotes N;
and with the proviso that compounds are excluded in which g is 0, W and M in each case denote C, P denotes N, Q denotes CR 16 and T denotes NR 19 ;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate and optionally one or more physiologically acceptable auxiliary substances.
28 . A pharmaceutical composition according to claim 27 comprising at least one compound of the formula Ie,
in which
R 1e denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2e , R 3e , R 4e , R 5e , R 6e and R 7e , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl;
ge denotes 0 or 1;
W e , M e , P e , Q e , T e and optionally V e together denote a ring selected from the group consisting of
and R 14e , R 16e , R 18e and R 20e , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
29 . A pharmaceutical composition according to claim 27 comprising at least one compound of the formula Ie1,
in which
R 1e denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 8e , R 9e , R 10e , R 11e , R 12e and R 13e , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl;
ge denotes 0 or 1;
W e , M e , P e , Q e , T e and optionally V e together denote a ring selected from the group consisting of
and R 14e , R 16e , R 18e and R 20e , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
30 . A pharmaceutical composition according to claim 27 , wherein
R 1e denotes a residue selected from the group consisting of phenyl, thienyl and pyridinyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; R 2e , R 3e , R 4e , R 5e , R 6e , R 7e , R 8e , R 9e , R 10e , R 11e , R 12e and R 13e , mutually independently, in each case denote H; methyl or ethyl; ge denotes 0 or 1; W e , M e , P e , Q e , T e and optionally V e together denote a ring selected from the group consisting of
and R 14e , R 16e , R 18e and R 20e , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl.
31 . A pharmaceutical composition according to claim 27 comprising at least one compound of the formula If,
in which
R 1f denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2f , R 3f , R 4f , R 5f , R 8f and R 9f , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl;
gf denotes 0 or 1;
W f , M f , P f , Q f , T f and optionally V f together denote a ring selected from the group consisting of
and R 14f , R 16 , R 18f and R 20 , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
32 . A pharmaceutical composition according to claim 27 comprising at least one compound of the formula If1,
in which
R 1f denotes a residue selected from the group consisting of phenyl, pyridinyl and thienyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, ethenyl, allyl, ethynyl, propynyl, cyclopropyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —NO 2 , —CF 3 , —CH 2 F, —CHF 2 , —O—CF 3 and —S—CF 3 ;
R 2f , R 3f , R 8f , R 9f , R 10f and R 11f , mutually independently, in each case denote H; F; Cl; Br; I; —NO 2 ; —CN; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —O—C 2 F 5 ; —O—CH 2 —CF 3 ; —CF 3 ; —CF 2 H; —CFH 2 ; —C 2 F 5 ; —CH 2 —CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; cyclopropyl or cyclobutyl;
gf denotes 0 or 1;
W f , M f , P f , Q f , T f and optionally V f together denote a ring selected from the group consisting of
and R 14f , R 16f , R 18f and R 20f , mutually independently, in each case denote H; F; Cl; Br; I; —CF 3 ; —NO 2 ; —CN; —NH 2 ; —OH; —C(═O)—OH; —C(═O)—H; —NH—CH 3 ; —N(CH 3 ) 2 ; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; —O—CF 2 H; —O—CFH 2 ; —C(═O)—O—CH 3 ; —C(═O)—O—C 2 H 5 ; —O—C(═O)—CH 3 ; —N(CH 3 )—C(═O)—CH 3 ; —C(═O)—NH 2 ; —C(═O)—NH—CH 3 ; —C(═O)—NH—C 2 H 5 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl; or denote a residue selected from the group consisting of phenyl and benzyl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl and tert.-butyl;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt or in each case in the form of a corresponding solvate.
33 . A pharmaceutical composition according to claim 31 , wherein
R 1f denotes a residue selected from the group consisting of phenyl, thienyl and pyridinyl, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert.-butyl, —OH, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CF 3 , —CN, F, Cl, Br and I; R 2f , R 3f , R 4f , R 5f , R 8f , R 9f , R 10e and R 11e , mutually independently, in each case denote H; methyl or ethyl; gf denotes 0 or 1; W f , M f , P f , Q f , T f and optionally V f together denote a ring selected from the group consisting of
and R 14 , R 16f , R 18f and R 20f , mutually independently, in each case denote H; F; Cl; Br; —OH; —O—CH 3 ; —O—C 2 H 5 ; —O—C(CH 3 ) 3 ; —O—CF 3 ; methyl; ethyl; n-propyl; isopropyl; n-butyl; 2-butyl; isobutyl; tert.-butyl or phenyl.
34 . A pharmaceutical composition according to claim 27 comprising at least one compound selected from the group consisting of
[1] 2-(3-phenyl-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[2] 1-(3-phenyl-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[5] 2-(3-(3-chlorophenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
2-(3-pyrid-2-yl-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[11] 2-(3-(3-chlorophenyl)-propiolyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,
[13] 2-(3-(3-chlorophenyl)-propiolyl)-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline,
[14] 6-methoxy-2-(3-phenyl-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6-hydroxy-7-methoxy-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline,
[18] 2-(3-(3-chlorophenyl)-propiolyl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-3-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-6-methyl-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3-chlorophenyl)-propiolyl)-7-methoxy-1,2,3,4-tetrahydro-isoquinoline,
[24] 2-(3-(3-chlorophenyl)-propiolyl)-8-methyl-1,2,3,4-tetrahydro-isoquinoline,
[25] 2-(3-(3-chlorophenyl)-propiolyl)-7-methyl-1,2,3,4-tetrahydro-isoquinoline,
[26] 2-(3-(3-chlorophenyl)-propiolyl)-5-methyl-1,2,3,4-tetrahydro-isoquinoline,
[28] 2-(3-(3-chlorophenyl)-propiolyl)-7-hydroxy-1,2,3,4-tetrahydro-isoquinoline,
[29] 2-(3-(3-chlorophenyl)-propiolyl)-8-methoxy-1,2,3,4-tetrahydro-isoquinoline,
[30] 2-(3-(3-chlorophenyl)-propiolyl)-5-methoxy-1,2,3,4-tetrahydro-isoquinoline,
[31] 2-(3-(3-chlorophenyl)-propiolyl)-1,8-dimethyl-1,2,3,4-tetrahydro-isoquinoline,
[32] 2-(3-(2,4-difluorophenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[34] 2-(3-(3-methoxyphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[35] 2-(3-(4-fluoro-3-methylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[37] 2-(3-(2-fluorophenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[39] 2-(3-(4-tolyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[41] 2-(3-(4-trifluoromethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[43] 2-(3-phenyl-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(2,3-dimethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(3,5-dimethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(2,4-dichlorophenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[51] 2-(3-(3-tolyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[53] 2-(3-(4-methoxyphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
2-(3-(2-thienyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[57] 1-(3-(4-tolyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[58] 1-(3-(4-trifluoromethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[59] 1-(3-(2,3-dimethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[60] 1-(3-(2,4-dichlorophenyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[61] 1-(3-(2,4-dimethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[62] 1-(3-(4-tert.-butylphenyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline,
[64] 2-(3-(4-fluorophenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[67] 2-(3-(3-fluoro-4-methylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[69] 2-(3-(4-tert.-butylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[71] 2-(3-(3,4-dimethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[76] 2-(3-(2-cyano-phenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[77] 2-(3-(3-cyano-phenyl)-propiolyl)-1,2,3,4-tetrahydro-isoquinoline,
[78] 1-(3-(2-tolyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline and
[79] 1-(3-(2-trifluoromethylphenyl)-propiolyl)-1,2,3,4-tetrahydro-quinoline;
in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any desired mixing ratio, or in each case in the form of a corresponding salts or in each case in the form of a corresponding solvate.
35 . (canceled)
36 . (canceled)
37 . (canceled)
38 . A method for mGluR5 receptor regulation comprising: administering an effective amount of at least one compound of claim 1 to a patient in need thereof.
39 . A method for the prevention, or treatment, or simultaneous prevention and treatment of disorders, or diseases, or disorders and diseases which are at least partially mediated by mGluR5 receptors comprising: administering an effective amount of at least one compound of claim 1 to a patient in need thereof.
40 . The method according to claim 39 , wherein the disorders or diseases are selected from the group consisting of pain; migraine; depression; neurodegenerative diseases; cognitive diseases; anxiety states; panic attacks; epilepsy; coughing; urinary incontinence; diarrhoea; pruritus; schizophrenia; cerebral ischaemic episodes; muscle spasms; cramps; pulmonary diseases; regurgitation (vomiting); stroke; dyskinesia; retinopathy; lack of drive; laryngitis); disorders of food intake; dependency on alcohol; dependency on medicines; dependency on drugs; alcohol abuse; abuse of medicines; drug abuse; withdrawal symptoms associated with dependency on alcohol, medicines and/or drugs; development of tolerance towards medicines; gastro-oesophageal reflux syndrome; gastro-oesophageal reflux disease; irritable bowel syndrome; diuresis; antinatriuresis; disorders of the cardiovascular system; reduced vigilance; reduced libido; and disorders related to locomotor activity.
41 . The method according to claim 40 , wherein the disorder or disease is selected from the group consisting of pain selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain; anxiety states; panic attacks; dependency on alcohol; dependency on medicines; cognitive diseases; disorders of food intake from the group consisting of bulimia, cachexia, anorexia and obesity; dependency on nicotine- and/or cocaine; alcohol abuse; abuse of medicines; nicotine and/or cocaine abuse; withdrawal symptoms associated with dependency on alcohol, medicines and/or nicotine- and/or cocaine; development of tolerance towards natural or synthetic opioids; gastro-oesophageal reflux syndrome, gastro-oesophageal reflux disease and irritable bowel syndrome.
42 . The method according to claim 40 , wherein the disorder or disease is pain selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain.
43 . The method according to claim 40 , wherein the disorder or disease is selected from the group consisting of anxiety states and panic attacks.
44 . A method of providing local anaesthesia to a patient in need thereof, said method comprising locally administering to said patient at least one compound according to claim 1 .Join the waitlist — get patent alerts
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